Sodium Hydroxide → HCID 178508859, compound

HRID 543888Notes

Reaction equation

HRID 543888 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([C:24]3[CH:45]=[CH:44][C:27]([C:28]([NH:30][C@H:31]([C:39]([O:41]CC)=[O:40])[CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[O:29])=[CH:26][CH:25]=3)[CH2:15][C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[CH:8]=2)[N:3]=1.[OH-].[Na+]>O.C(O)C>[NH2:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([C:24]3[CH:25]=[CH:26][C:27]([C:28]([NH:30][C@H:31]([C:39]([OH:41])=[O:40])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:29])=[CH:44][CH:45]=3)[CH2:15][C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178471581HCID 178471581, compound

Product 1

HCID 178508859HCID 178508859, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Diethyl N-(4-(N-(2-amino-4-hydroxy-6-quinazolinyl)methyl-N-(5-uracilyl)methyl-amino)benzoyl)-L-glutamate (0.327 g) was suspended in a mixture of water (7 ml) and ethanol (2 ml) and treated with 1 N NaOH aq. (6 mol. eq.) Vigorous shaking gave a solution within 30 min. After a further 1.5 hr. the solution was clarified by filtration and the pH brought to 4.0 using 1 N HCl aq. A particulate precipitate of the product resulted. It was freed from inorganic ions by three cycles of suspension-centrifugation-decantation. The amorphous white solid was dried at 40° C. in vacuo, to yield the pure diacid, N-(4-(N-(2-amino-4-hydroxy-6-quinazolinyl)methyl-N-(5-uracilyl)methyl-amino)benzoyl)-L-glutamic acid (CB 3743), as its dihydrate (68%), m.p. 250°-255° C. The structure was confirmed by elemental analysis (C,H,N) and by uv spectroscopy (spectrum determined in 0.1 N NaOH eq.). λ(nm) (ε) maxima: 310 (29,200), 276.5 (22,000), 230 (50,700); minima: 282.5 (21,500), 251.5 (11,600).

Workup

  1. customgave a solution within 30 min
  2. filtrationthe solution was clarified by filtration
  3. customresulted
  4. customThe amorphous white solid was dried at 40° C. in vacuo

Sources & evidence

ORD record
ord-d972dcee9da249659ff64d4f90322b72
Source dataset
uspto-grants-1984_05
Patent number
US04447608

Reaction notes

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